5-S-octyl-5-thio-D-ribono-1,4-lactone | 386744-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-S-octyl-5-thio-D-ribono-1,4-lactone
• 英文别名: (3R,4S,5S)-3,4-dihydroxy-5-(octylsulfanylmethyl)oxolan-2-one
• CAS: 386744-02-1
• 化学式: C₁₃H₂₄O₄S
• 分子量: 276.397
• InChiKey: SFUWDNNDIBANQH-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-S-octyl-5-thio-D-ribono-1,4-lactone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以0.19%的产率得到1-S-octyl-1-thio-L-ribitol
  参考文献：
  名称：

  Efficient syntheses of 1-S-alkyl-1-thio-l-ribitols, d-lyxitols and l-xylitols from d-pentono-1,4-lactones

  摘要：

  The thioalkylation of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono, and D-xylono-1,4-lactone was performed with the alkylthiol-sodium hydride reagent. The corresponding 5-S-alkyl-5-thio-D-pentono-1,4-lactones were isolated in good yields (82-95%). Reduction with NaBH4 of these derivatives gave the 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols in 85-96% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00204-x
• 作为产物：
  描述：

  1-辛硫醇 、 5-bromo-5-deoxy-D-ribono-1,4-lactone 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.08h， 生成 5-S-octyl-5-thio-D-ribono-1,4-lactone
  参考文献：
  名称：

  烷基链长度对5-S-烷基-5-硫代戊内酯和5-S-烷基-5-硫代戊糖醇的同晶型的影响。

  摘要：

  研究了S-烷硫基戊内酯（d-核糖基，d-阿拉伯糖基和d-木糖基）和相应的通式为Su-SR（R = CnH2n + 1； n = 5-12）的糖醇衍生物的介晶性质。结果表明，热致相变温度受以下结构参数的影响：烷基链长，环状或无环Su结构和糖醇构象。此外，似乎n平价会影响热致相变温度。

  DOI：

  10.1016/j.carres.2014.04.008

文献信息

• Influence of alkyl chain length on the mesomorphism of 5-S-alkyl-5-thiopentonolactones and 5-S-alkyl-5-thiopentitols
  作者：Imane Stasik、Sébastien Gottis、Céline Falentin-Daudré、Claire Meyer

  DOI：10.1016/j.carres.2014.04.008

  日期：2014.6

  (d-ribono, d-arabinono and d-xylono) and corresponding alditol derivatives with the general formula Su-SR (R=CnH2n+1; n=5-12) are studied. It was shown that the thermotropic and lyotropic phase transition temperatures are influenced by the following structural parameters: alkyl chain length, cyclic or acyclic Su structure and alditol conformation. Besides, it seems that n parity affects thermotropic

  研究了S-烷硫基戊内酯（d-核糖基，d-阿拉伯糖基和d-木糖基）和相应的通式为Su-SR（R = CnH2n + 1； n = 5-12）的糖醇衍生物的介晶性质。结果表明，热致相变温度受以下结构参数的影响：烷基链长，环状或无环Su结构和糖醇构象。此外，似乎n平价会影响热致相变温度。
• Efficient syntheses of 1-S-alkyl-1-thio-l-ribitols, d-lyxitols and l-xylitols from d-pentono-1,4-lactones
  作者：Jérôme Lalot、Gaëtane Manier、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/s0008-6215(01)00204-x

  日期：2001.9

  The thioalkylation of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono, and D-xylono-1,4-lactone was performed with the alkylthiol-sodium hydride reagent. The corresponding 5-S-alkyl-5-thio-D-pentono-1,4-lactones were isolated in good yields (82-95%). Reduction with NaBH4 of these derivatives gave the 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols in 85-96% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.